1,4,5,8,9,10-hexahydro-2(3H)-anthracenone | 133374-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,4,5,8,9,10-hexahydro-2(3H)-anthracenone
• 英文别名: 3,4,5,8,9,10-hexahydro-1H-anthracen-2-one
• CAS: 133374-37-5
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: OGRICGVYURPYHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4,5,8,9,10-hexahydro-2(3H)-anthracenone 在 高氯酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以72%的产率得到4,4a,5,6,10,10a-hexahydro-2(3H)-anthracenone
  参考文献：
  名称：

  Thermal cis-trans rearrangement of semirigid polyenes as a model for the anticarcinogen .beta.-carotene: an all-trans-pentaene and an all-trans-heptaene

  摘要：

  To assess the possible role of a 15,15' 90-degrees-twisted, singlet diradical in the anticarcinogenicity of beta-carotene, activation parameters for the thermal, cis-trans interconversion of all-trans-beta-carotene (1) and 15,15'-cis-beta-carotene (2), polyenes of order 11, are needed. Indirect achievement of this goal is initiated here by determining activation parameters for cis-trans rearrangement in a set of semirigid, all-trans-polyenes of order 3, 5, and 7 (9 to follow). These data also provide a test of theoretical calculations of stabilization energies of polyenyl radicals. For the coherent series, 3(1,1,1), 5(2,1,2), and 7(3,1,3), these activation parameters (DELTA-H double-ended-dagger (kcal/mol), DELTA-S double-ended-dagger (cal/mol.K)) are found: 38.9, -6.0; 32.1, -4.4; 27.5, -4.4. The trend is a diminishing return as the order is increased. ''Stabilization energies'', defined as extra stabilization associated with delocalization of the odd electron and derived with allyl as the reference point (SE1 = 13.5 kcal/mol), are pentadienyl, SE2 = 16.9 kcal/mol, and heptatrienyl, SE3 = 19.2 kcal/mol. Heptaene 7 rearranges in a range, 64-104-degrees-C, that is close enough to 37-degrees-C to forewarn of thermal lability of beta-carotene in cell membranes.

  DOI：

  10.1021/ja00011a036
• 作为产物：
  描述：

  1,4,5,8,9,10-hexahydro-2-methoxyanthracene 在 高氯酸 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以100%的产率得到1,4,5,8,9,10-hexahydro-2(3H)-anthracenone
  参考文献：
  名称：

  Thermal cis-trans rearrangement of semirigid polyenes as a model for the anticarcinogen .beta.-carotene: an all-trans-pentaene and an all-trans-heptaene

  摘要：

  To assess the possible role of a 15,15' 90-degrees-twisted, singlet diradical in the anticarcinogenicity of beta-carotene, activation parameters for the thermal, cis-trans interconversion of all-trans-beta-carotene (1) and 15,15'-cis-beta-carotene (2), polyenes of order 11, are needed. Indirect achievement of this goal is initiated here by determining activation parameters for cis-trans rearrangement in a set of semirigid, all-trans-polyenes of order 3, 5, and 7 (9 to follow). These data also provide a test of theoretical calculations of stabilization energies of polyenyl radicals. For the coherent series, 3(1,1,1), 5(2,1,2), and 7(3,1,3), these activation parameters (DELTA-H double-ended-dagger (kcal/mol), DELTA-S double-ended-dagger (cal/mol.K)) are found: 38.9, -6.0; 32.1, -4.4; 27.5, -4.4. The trend is a diminishing return as the order is increased. ''Stabilization energies'', defined as extra stabilization associated with delocalization of the odd electron and derived with allyl as the reference point (SE1 = 13.5 kcal/mol), are pentadienyl, SE2 = 16.9 kcal/mol, and heptatrienyl, SE3 = 19.2 kcal/mol. Heptaene 7 rearranges in a range, 64-104-degrees-C, that is close enough to 37-degrees-C to forewarn of thermal lability of beta-carotene in cell membranes.

  DOI：

  10.1021/ja00011a036

文献信息

• DOERING, W. E. VON;KITAGAWA, TOSHIKAZU, J. AMER. CHEM. SOC., 113,(1991) N1, C. 4288-4297
  作者：DOERING, W. E. VON、KITAGAWA, TOSHIKAZU

  DOI：——

  日期：——